Considered as a misfit in his own time, Oscar Wilde (1854-1900) has an idiosyncratic perspective that defies the traditional regulations and social norms of the Victorian era. Witnessing the gradual disintegration of the moral values and the hypocritical practices of the late Victorian society, Wilde develops a humorous attitude which enables the reader/audience to question the ambivalent gaps between ‘sharp’ distinctions – such as good and bad, honest and corrupt, pure and fallen – in his works. Rejecting the status of art as an instrument of moral education that aims to guide the society, Wilde refrains from applauding the long-established values of the Victorian upper and upper-middle classes. Instead, he tries to draw attention to the hidden layers of meaning that bring the hypocritical agenda of the Victorian morals to the surface. In this respect, it is to be argued that illustrating the grey areas between Lady Windermere who, as a devout wife, was about to cross the line between a ‘good’ and a ‘bad’ woman if it were not for the altruism of her mother, and Mrs Erlynne, who is the so-called ‘bad’ woman with an unknown past, Wilde’s Lady Windermere’s Fan (1892) illustrates the interchangeable points between either/or dualities. Therefore, this paper intends to analyse the remoulding of the strict Victorian binaries – which have long been constructed in accordance with the hypocritical premises of the late 19th century in England. In addition, although the main scope of this study is not concerned with applying a postmodern or feminist reading to the source text, in order to support Wilde’s intention to problematize the constructed status of the binary oppositions, Julia Kristeva’s (b. 1941) criticism against the patriarchal representation of women will also be touched upon.